Chlor-methyl-omega-brom-propyl-carbinol and process of producing same.



UNITED, sTATEs PATE T oFFIoE.

ALEX IB. DAvIs, or rNDrANAroLIs, INDIANA, .ASSIGNOR TO THE ELI LILLY AND COMPANY, or INDIANAPOLIS, INDIANA, A CORPORATION or INDIANA.

CHLOB-METHYL-OMEGA-BROlllI-PROPYL-CARBINOL AND PROCESS OF PRODUCING SAME.

No Drawing.

Specification of Letters Patent.

Application filed July 14, 1913. Serial No. 778,883.

Patented Oct. 27, 1914.

To all whom it may concern:

Be it known that I, ALEX B. DAVIS, a citizen of the United States, residing at Indianapolis, Marion county, and State of Indiana, have invented and discovered certain new and useful Improvements in Chlor- Methyl-Omega-Brom Propyl Carbinol and Processes of Producing Same, of which the following is a specification.

The invention relates to the hitherto unknown chlor methyl omega brom propylcarbinol to which may be ascribed the forp mula ' ClCHr-(iI-CH -CH -CHgBl' It is a valuable intermediate product in the preparation of other compounds. To produce this-comp0und ethylene bromid is converted into brom-ethyl-magnesium-bromid by dissolving one molecular proportion of magnesium in an absolute ethereal solution of ethylene bromid, and adding to this one molecular proportion of epichlorhydrin. The bromethyl -magnesiu m"-bromid condenses with the. epichlorhydrin to form a magnesium derivative of the new carbinol, which is then'decomposed' by acids liberating the new compound.

The process in detail may be carried out as follows: 188 grams of ethylene bromid are mixed with 300 0. c. of absolute ether and placed in a flask connected to a reflux condenser. 24 grams of magnesium in the form of ribbon, turnings, wire or othersuitable .form are added gradually through the condenser, one or two grams at a time. The

magnesium dissolves rapidly producing a compound of the formula BrCHs-CHaMgBrO tive of the new carbinol. 'After standing a short time, this solidifies to a mass of nearly white crystals. The crystalline mass thus obtained is mixed with powdered ice and acidified with dilute sulfuric acid. A layer consisting of the new compound in solution in ether separates and is drawn 0d, the ether evaporated and the residue distilled in vacuum, when it boils at 100 C., under 20m. In.

pressure and has the formula cicm-d-cm-cm-cnmr 2. The process of producing a carbinol by condensing brom-ethyl-magnesium, bromid with epichlorhydri-n.

3. The process of producing acarb'inol by I condensing brom-ethyl magnesium bromid of the following formula BrCH -CH MgBr with epichlorhydrin of the following formula v Y n o CHQGH-CHKJI 4. The process of producing chlor-methylomega-brom-propyl-carbinol which consists in dissolving one molecular proport1on of magnesium in an absolute ethereal solution of ethylene bromid, and addin one molecular proportionof epichlorhy rin and then: decomposing the derivative by an acid suitable for'liberating the carbinol.

In witness whereof, I have-hereunto set my hand and seal at Indiamgolis, Indiana,

this thirtieth day of June, D. nineteen hundred and thirteen.

' ALEXB. DAVIS. [L.s.] Witnesses:

FRANK R. Erpaao',

RHODLBA'ND. 

